WO2009136561A1 - Procédé de fixation d'agent antibactérien et article obtenu par le procédé - Google Patents

Procédé de fixation d'agent antibactérien et article obtenu par le procédé Download PDF

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Publication number
WO2009136561A1
WO2009136561A1 PCT/JP2009/058229 JP2009058229W WO2009136561A1 WO 2009136561 A1 WO2009136561 A1 WO 2009136561A1 JP 2009058229 W JP2009058229 W JP 2009058229W WO 2009136561 A1 WO2009136561 A1 WO 2009136561A1
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Prior art keywords
antibacterial agent
group
antibacterial
ammonium chloride
chloride
Prior art date
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PCT/JP2009/058229
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English (en)
Japanese (ja)
Inventor
浩樹 二川
Original Assignee
国立大学法人広島大学
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Application filed by 国立大学法人広島大学 filed Critical 国立大学法人広島大学
Priority to EP09742685.2A priority Critical patent/EP2274985A4/fr
Priority to US12/736,794 priority patent/US8859009B2/en
Priority to CN2009801270768A priority patent/CN102105062A/zh
Priority to JP2010511046A priority patent/JP5618370B2/ja
Priority to AU2009245152A priority patent/AU2009245152B2/en
Priority to KR1020107027749A priority patent/KR101681522B1/ko
Publication of WO2009136561A1 publication Critical patent/WO2009136561A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/162—Organic compounds containing Si
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions

Definitions

  • Patent application title Method for immobilizing antibacterial agent and article obtained by the method
  • the present invention relates to an antibacterial agent immobilization method capable of imparting excellent antibacterial property and antibacterial persistence to a product as well as excellent washability, and an article obtained by the method. .
  • the antibacterial compositions used in these are categorized by component system. Peroxides, hypochlorous acid, enzymes, acids, crude drugs, silver-based inorganic antibacterial agents or disinfectants are the main components. It can be classified into component systems combining more than one species. And even though the antibacterial composition belongs to the same component system, its specific composition varies.
  • an antibacterial composition is often composed of a combination of components that exhibit their respective actions.
  • Patent Document 1 discloses that sodium lauryl sulfate has an excellent cleaning ability and foaming action. Containing sodium lauryl sulfate and antibacterial metal ions such as silver, copper, and zinc ions that do not interfere with the function of sodium lauryl sulfate and can improve sterilization performance. Denture cleaning agent It is disclosed.
  • acid denture lj is preferable for removing denture plaque, but if denture cleaner is acidic, the gum material may be deformed or discolored and the metal material may turn black.
  • the acid fast-dissolving part containing acid and persulfate and the perborate or A granular or tablet-like denture cleaning agent containing at least one percarbonate and a carbonate-containing alkaline slow-dissolving part, which is blended in denture cleaning water to reduce the liquidity of the water from low to high pH Denture washing that can be changed to
  • antibacterial substances such as octadecinoletrimethoxysilane, ⁇ -aminopropinoretriethoxysilane, and octadecyldimethyl (3-trimethoxysilylpropyl) ammonium chloride are immobilized on the surface. It is also disclosed that it can be used in dental applications such as dentures, implants, crowns, bridges, orthodontic brackets, wires, etc.An antibacterial composition itself containing these antibacterial components is disclosed Not.
  • an antibacterial agent having improved washing ability and bactericidal performance can be obtained.
  • conventional antibacterial agents can be used to clean and clean dental materials such as dentures, implants, crowns, bridges, orthodontic brackets, and dental wires.
  • the denture plaque was formed again on the denture surface during use (there was a problem that SJh could not be done.
  • the cleaning performance of dental materials, especially the denture cleaning ⁇ improved the vitality Antibacterial agents are required, and also for dishes, glasses, sinks, kitchens, toilets, toilets, bathtubs, bathrooms, toilet bowls, toilets, and antibacterial washing for textile products or clothes. The same antibacterial performance, cleansing ability and sustainability are required. [0 0 0 9]
  • Patent Document 4 aims to improve the cleaning performance and sterilization performance, and also improve the antibacterial performance, cleaning performance, and the performance of the cleaned object to be cleaned.
  • Dental materials such as bridges, orthodontic brackets, and dental wires
  • a detergent composition that has antibacterial and cleansing capabilities that can relieve denture plaque from re-forming on the denture surface while it is installed in the oral cavity.
  • the purpose is to:
  • Another object of the present invention is to provide a denture washing composition that can easily impart antibacterial performance to dentures without causing any particular burden or discomfort to denture users.
  • Patent Document 4 describes antibacterial performance and washing performance for dishes, glasses, sinks, kitchens, toilets, toilets, bathtubs, bathrooms, wash bowls, washrooms, textile products and clothes. It is also intended to produce washed U yarn that can meet the demands of its life!
  • Patent Document 3 Japanese Unexamined Patent Application Publication No. 2004-209241
  • Patent Document 4 Japanese Unexamined Patent Application Publication No. 2007-146134
  • an object of the present invention is to provide an antibacterial agent immobilization method capable of imparting an excellent antibacterial performance and its sustained I "life to an article made of a wide range of materials.
  • the major feature of the silicon-containing compound antibacterial agent used in the process is chemical bonding to the surface of the article to be treated. The point is that it is fixed. This will be described below.
  • the chemical reaction formula shown below is an example of a compound containing silicon used in the present invention.
  • E t AC Antibacterial composition containing octadeci / redimethyl (3-triethoxysilylpropyl) ammonium chloride
  • An example of immobilization using an object is shown. That is, when E t AC is applied to the surface of the article to be treated, oxygen-containing functional groups (one OC 2 H 5 : ethoxy group), which is a foot when immobilizing E t AC, are formed on the surface of the article to be treated. It reacts with oxygen-containing functional groups to release ethanol and covalently bonds via oxygen. As a result, a compound containing silicon on the surface of the article to be processed
  • the present inventor performed a surface treatment for imparting an oxygen-containing functional group to the surface of an article before performing the treatment using the antibacterial agent composition.
  • the article is made of a synthetic resin
  • the present inventors have found that the antibacterial performance and its sustainability ((3) life can be imparted) have been completed.
  • the method for immobilizing an antibacterial agent of the present invention comprises subjecting the surface of the article to surface treatment for imparting an oxygen functional group,
  • R 1 represents a hydrocarbon group having 6 or more carbon atoms
  • R 2 and R 3 may be the same or different and represent a lower hydrocarbon group
  • R 4 represents a divalent lower carbon group.
  • a hydrogen group, R 5, R 6 and R 7 are the same or different and may represent a lower alkyl group or a lower alkoxy group
  • X represents a halogen ion or an organic carboquinoxy ion. It is characterized by performing a treatment using an antibacterial agent composition containing a represented compound containing silicon.
  • the surface treatment may be ozone water treatment or 1 to: I 0 GHz microphone mouth wave irradiation treatment.
  • an article is obtained by: (a)-general formula (1)
  • R 1 represents a hydrocarbon group having 6 or more carbon atoms
  • R 2 and R 3 may be the same or different and represent a lower hydrocarbon group
  • R 4 represents a divalent lower carbon group
  • R 5, R 6 and R 7 may be the same or different lower alkynole group or lower alkoxy group
  • X represents a halogen ion or an organic carboquinoxy ion.
  • the antibacterial agent composition further comprises: (b) a cationic surface active dejugating agent (however, excluding the above-mentioned key compound) (bl), a nonionic surface active It is desirable to include at least one surfactant selected from the group consisting of agent (b 2) and amphoteric surfactant (b 3) force.
  • R 1 of the silicon-containing compound (a) represented by the general formula (1) represents an alkyl group having 10 to 25 carbon atoms
  • R 2 and R 3 may be the same or different and each represents a lower alkyl group having 1 to 6 carbon atoms
  • R 4 represents a lower alkylene group having 1 to 6 carbon atoms
  • R 5, R 6 and R 7 represents a lower alkyl group having 1 to 6 carbon atoms or an alkoxy group, which may be the same or different
  • X is preferably a halogen ion or an organic carboquinoxy ion. [0 0 2 4]
  • the silicon-containing compound (a) represented by the general formula (1) octadecinoredimethyl (3-trimethoxysilylpropyl) ammonium chloride , Octadecyldimethyl (3-triethoxysilylpropyl) ammonium chloride, Octadecyljetyl (3-trimethoxysilylpropyl) ammonium chloride, Octadecyldimethyl (2-trimethylsilylethyl) ammonium chloride, o Kutadecyldipropyl (4-trimethoxysilylbutyl) ammonia Acetate, octadecinoledimethyl (3-triisopropoxysilylpropyl) ammonium chloride, octadecyldimethyl (3-triethylsilylsilylpropyl) ammonium chloride, octadecinoledimethyl (3 —Trifluoride, octadecinoledimethyl (3-
  • the cationic surfactant (b 1) is represented by the following general formula (2)
  • R 1 1 represents a hydrocarbon group having 6 or more carbon atoms
  • R 1 2, R 1 3 and R 14 represent a lower hydrocarbon group which may be the same or different
  • Y represents a halogenion or It is desirable to be a cationic surfactant (b 1 1) represented by the formula:
  • R 11 of the ftit self-cationic surfactant (b 1 1) represented by the general formula (2) is 10 to 25 carbon atoms.
  • R 12, R 13 and R 14 are the same or different lower alkyl groups having 1 to 6 carbon atoms, and Y is a halogenoion or an organic carbonyloxyion. May be.
  • the cationic surfactant (b 1 1) force hexadecyltrimethylammonium chloride, decyltrimethylammonium chloride, decyltriethylammonium acetate, Decinole trimethyl ammonium acetate, dodecinole triisopropyl ammonium bromide, tridecyl triethyl ammonium chloride, tetradecinole trimethyl ammonium chloride, tetradecinole triethyl ammonium chloride, tetradecyl tree n-propyl ammonium chloride, pentadecyltrimethylammonium chloride, pentadecyltriethylammonium chloride, pentadecinoretriol n-propynoleammonium chloride, hexadesi From the group consisting of triethylammonium chloride, pentadecyltriethylammonium chloride, pentadecinore
  • the cationic surfactant (b 1) is N-cocoyl monoarginine ester pyridone carboxylate (b 1 2) or cetinorepyridini. It may be um salt (b 1 3).
  • the nonionic surfactant (b 2) is an alkyl ether of a polyoxyalkylene glycol containing polyoxyethylene units and Z or polyoxypropylene units, or Fatty acid ester, Sorbitan fatty acid ester, Fatty acid monoglyceride, Fatty acid ester, Fatty acid alcohol amide, Luminic acid amide, Alkyl ether, Alkylamine oxide, Polyoxyethylene alkyl ether and Polyoxyethylene noel phenyl ether Desirably, the nonionic surfactant is at least one selected from the group.
  • the nonionic surfactant (b 2) is preferably polyoxyethylene sorbitan monolaurate.
  • the amphoteric surfactant 1 to herbal agent (b 3) is at least one selected from the group consisting of betaines and amine oxides. It's preferable to
  • the zwitterionic surfactant (b 3) is lauramide propinole dimethylamine oxide or lauryl dimethylamine oxide. preferable.
  • the article of the present invention is characterized in that the antibacterial agent is immobilized on the surface by the antibacterial agent immobilization method.
  • the present invention it is possible to fix a compound containing a compound to a synthetic resin-based article or the like that has been difficult to immobilize conventionally. It has the antibacterial performance and the lj effect that it can be given.
  • FIG. 2 is a graph showing the results 12 hours after the start of culture in an antibacterial individual test of a test piece treated with ozone water for 0, 1, 3, 5 or 10 minutes and then fixed with an antibacterial agent.
  • FIG. 3 This figure shows the results after 18 hours from the start of culture in the antibacterial test of test pieces that were treated with ozone water for 0, 1, 3, 5, 10 minutes and then fixed with antibacterial agent. is there.
  • FIG. 4 is a graph showing the results after 36 hours from the start of culture in an antibacterial individual test of a test piece that was treated with ozone water for 0, 1, 3, 5, 10 minutes and then fixed with an antibacterial agent.
  • FIG. 5 is a graph showing the results 48 hours after the start of culture in the antibacterial test of test pieces that were treated with ozone water for 0, 1, 3, 5, 10 minutes and then fixed with an antibacterial agent.
  • FIG. 6 This figure shows the results one week after the start of culturing in the antibacterial test of test pieces that were treated with ozone water for 0, 1, 3, 5, 10 minutes and then fixed with an antibacterial agent. is there.
  • FIG. 7 is a diagram showing the results 33 hours after the start of culture in an antibacterial test of a test piece subjected to antibacterial agent immobilization treatment using each solution in Example 3.
  • FIG. 8 Antibacterial test of a test piece subjected to antibacterial agent immobilization treatment using each solution in Example 3. In the experiment, it is a figure which shows the result 45 hours after the culture start.
  • the method for immobilizing an antibacterial agent according to the present invention includes a surface treatment for imparting oxygen-containing functional groups to the surface of an article, and
  • R 1 represents a hydrocarbon group having 6 or more carbon atoms
  • R 2 and R 3 may be the same or different and represent a lower hydrocarbon group
  • R 4 represents a divalent lower hydrocarbon
  • R 5, R 6 and R 7 represent a lower alkyl group or a lower alkoxy group which may be the same or different
  • X represents a halogen ion or an organic carboquinyloxy ion.
  • the surface treatment may be any treatment that imparts an oxygen-containing functional group such as 1 O— or 1 OH to the surface of the article.
  • the surface treatment may be ozone water treatment or microwaves of 1 to 10 GHz.
  • Irradiation treatment is a suitable treatment.
  • the article to be cleaned is first treated with the antibacterial agent thread and the composition, and then the antibacterial agent composition remains on the surface of the article.
  • surface treatment by microwave irradiation of 1 to 10 GHz may be performed, and an equivalent effect can be obtained.
  • the surface of the article is subjected to a surface treatment for imparting an oxygen-containing functional group, for example, by an ozone water treatment or a microphone mouth wave irradiation treatment of 1 to 10 GHz, and then the antibacterial agent composition.
  • the antibacterial yarn I ⁇ is applied to the surface of the article, and then the antibacterial agent composition is left on the surface of the article, and the microwave mouth wave irradiation treatment of 1 to 10 GHz is performed. Therefore, the above-mentioned compound containing a silicon which is an antibacterial component contained in the antibacterial agent composition on the surface of the article.
  • the article can be imparted with excellent antibacterial performance and its production.
  • the treatment with ozone water is not particularly limited.
  • the surface of the article may be formed by immersing the article in ozone water adjusted in concentration or by spraying ozone water on the article or by applying the article. This can be done by translating into ozone water.
  • the treatment time with ozone water can be changed as appropriate depending on the concentration of ozone water used. For example, when the ozone concentration is 0.4 to 0.6 ppm, the immersion treatment may be performed for about 5 minutes. In the case of normal ozone water with a concentration of several ppm, it is possible to impart sufficient antibacterial performance and sustainability to an article by simply spraying and natural drying treatment.
  • the hydrogen portion in the hydrocarbon is radicalized to generate oxygen-containing functional groups (one OH, one C HO, etc.), and the oxygen-containing functional group on the surface of the article. It is conceivable that, by improving the reactivity with the antibacterial component in the antibacterial agent composition, it is possible to impart higher antibacterial performance and improved life to the article. [0 0 4 1]
  • the microwave irradiation treatment of 1 to 1 O GHz is not particularly limited, but is preferably a treatment using a microwave oven.
  • An article is placed in a microwave oven, and the microwave is irradiated by the microwave oven.
  • a microwave oven is a “cooking device that heats food by applying high-frequency electromagnetic waves,” and generally heats food by irradiating microwaves with a wavelength of 2.45 O GHz.
  • Including equipment ⁇ ! ⁇ As a microwave irradiation method either a batch type or a continuous type may be used.
  • Examples of the microwave oven that can be used in the present invention include a home microwave oven, a high-power commercial microwave oven, and an industrial microwave accelerator.
  • sufficient effect can be acquired by processing for 30 seconds with an output of 700W. After performing the above, a sufficient effect can be obtained in 700W for 20 seconds and 500W in 30 seconds. That is, by irradiating the product with microwaves, the atoms on the surface of the product are excited and react with oxygen in the atmosphere to form oxygen-containing functional groups. Reacts with oxygen to produce oxygen-containing functional groups. In this way, the microphone An oxygen-containing functional group is generated by irradiating the mouth wave.
  • the above-mentioned ozone water treatment the power that can achieve the effect of the present invention even if any of the microphone mouth wave irradiation treatments of 1 to: I 0 GHz is used. Even large products can be processed easily, and products are manufactured on the factory line, and when the antibacterial agent fixing method of the present invention is used to impart antibacterial performance to the product, it is easy to incorporate into the line. .
  • Microwave treatment can be used for microwave irradiation treatment of 1 to 10 GHz, and the effect of the present invention can be obtained even in a home microwave oven. There is an advantage that the agent fixing method can be carried out.
  • the silicon-containing compound (a), which is an antibacterial component contained in the above antibacterial agent composition, is represented by the general formula (1)
  • R 1 represents a hydrocarbon group having 6 or more carbon atoms
  • R 2 and R 3 are the same or different, and may represent a lower hydrocarbon group
  • R 4 represents a divalent lower group.
  • R 5, R 6 and R 7 represent the same or different lower alkyl group or lower alkoxy group
  • X represents a halogen ion or an organic carbonyloxy ion (organic carboxylate ion).
  • the antibacterial agent composition may contain one or more types of the key compound containing compounds represented by the general formula (1).
  • R 1 in the general formula (1) is an alkyl group having 10 to 25 carbon atoms.
  • R 2 and R 3 may be the same or different and represent a lower alkyl group having 1 to 6 carbon atoms.
  • R 4 represents a lower alkylene group having 1 to 6 carbon atoms,
  • R 5, R 6 and R 7 may be the same or different, and a lower alkyl group having 1 to 6 carbon atoms or a lower alkoxy group.
  • X represents a silicon-containing compound which is a halogen ion or an organic carbonyloxy ion (organic carbonate ion).
  • the hydrocarbon group having 6 or more carbon atoms of R 1 includes hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, Examples include heptadecyl group, octadecyl group, nonadecyl group, eicosyl group, uneicosyl group, doeicosyl group, trieicosyl group, tetraeicosyl group, pentaeicosyl group and the like.
  • Examples of the lower hydrocarbon group which may be the same or different for R 2 and R 3 include, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a pentyl group, a hexyl group, a cyclohexyl group, Examples thereof include a phenyl group and a tolyl group.
  • Examples of the lower alkylene group for R 4 include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, and a hexamethylene group.
  • R 5, R 6 and R 7 may be the same or different lower alkyl group or lower alkoxy group, and specifically include a methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, pentyloxy group. Hexyl / reoxy group, methyl group, ethyl group, propyl group, isopropyl group, butyl group, pentyl group, hexyl group and the like can be exemplified. [0 0 5 1]
  • X is a halogen ion such as chlorine ion or bromine ion, methyl carbonate ⁇ / oxy ion (acetate ion), ethylcarbonyloxy ion (propionate ion), phenylcarbonyloxy ion (benzoate ion) Examples thereof include organic carbonyloxy ions (organic carboxylate ions).
  • the following compounds can be exemplified as the silicon-containing compound (a).
  • the antibacterial agent composition includes, in addition to the above-mentioned key compound, a cationic surfactant (excluding the above key compound) (bl), a non-ionic surfactant (b 2) and both Surfactant (b 3) At least one surfactant selected from the group consisting of forces can be contained.
  • the cationic surfactant (b) is a cationic surfactant represented by the following general formula (2), except that it is a cationic surfactant (b 11) excluding the key compound (a). is there
  • Rl 1 represents a hydrocarbon group having 6 or more carbon atoms
  • R12, shaku 13 shobi! 1 4 represents a lower hydrocarbon group which may be the same or different.
  • cetinorepyridinum salt (b l 3) such as a salt cetinorepyridinium.
  • R 11 represents an alkyl group having 10 to 25 carbon atoms
  • R12, R13, and R14 are the same.
  • Y is a halogen ion or an organic carbonyloxy ion (organic carboxylate ion).
  • the hydrocarbon group R 1 1 having 6 or more carbon atoms may be represented by the general formula (1) of the above-mentioned key compound (a). Examples of the hydrocarbon group having 6 or more carbon atoms exemplified as R1 in the above can be similarly exemplified.
  • Rl 2, R 13 and R14 of the cationic surfactant (b 11) represented by the above general formula (2) include R 2 and R 3 of the general formula (1)
  • cationic surfactant (b11) represented by the general formula (2) include the following compounds. Hexadecino trimethyl ammonium chloride, Decino trimethyl ammonium chloride, Decinotriethyl ammonium ammonium acetate, Dodecyl trimethyl ammonium ammonium acetate, Dodecyl triisopropyl ammonium bromide, Tri Decyltriethylammonium promide, tetradecyltrimethylammonium chloride, tetradecyltriethylammonium chloride
  • Tetradecyltri-n-propyl ammonium chloride pentadecyltrimethyl ammonium chloride, pentadecinoletriethyl ammonium chloride, pentadecinotriethyl n-propylammonium chloride, hexadecinretriethyl ammonium chloride Muchloride, hexadecinoletri-n-propyl ammonium chloride, octadecyltrimethylammonium chloride and octadecyltriethylammonium chloride And n-propynoleammonium chloride, and hexadecyltrimethylammonium is the most preferred.
  • the nonionic surfactant 14 agent (b 2) is an alkyl ether or a fatty acid ester of a polyoxyalkylene glycol containing a polyoxyethylene unit or a nopolyoxypropylene pyrene unit, a sorbitan fatty acid ester, a fatty acid monodaride, a fatty acid alkanolamide. And at least one nonionic surfactant selected from the group consisting of fatty acid amides, alkyl ethers, alkylamine oxides, polyoxyethylene alkyl ethers and polyoxyethylene noel phenyl ethers.
  • nonionic surfactant 14 agent (b 2) examples include monoalkyl ethers of polyethylene glycol, monoanolalkyl ethers of polyalkylene glycols containing both polyoxyethylene units and polyoxypropylene units, Sonolebitan laurate, polyoxyethylene sorbitan monolaurate, lunar fatty acid monoglyceride, fatty acid ester, fatty acid alcohol amide, fatty acid amide, alkyl ether, alkylamine amide, polyoxyethylene alkyl etherole and polyoxyethylene ureol
  • An example is at least one nonionic surfactant selected from the group consisting of diethers.
  • nonionic surfactant examples include sorbitan fatty acid esters such as sorbitan monolaurate and sorbitan sesquiisostearate; glycerin fatty acid esters such as glycerin monooleate and glycerin monoisostearate; diglyceryl mono Polyglycerin fatty acid esters such as oleate and decaglyceryl diisostearate; polyoxyethylene sorbitan fatty acid esters such as polyoxyethylene sorbitan monooleate and polyoxyethylene sorbenomonolate; polyoxyethylene sorbitan mono Polyoxyethylene sorbite fatty acid esters such as laurate and polyoxyethylene sorbit tetraoleate; polyoxyethylene glyceryl monooleate, polyoxyethylene glyceryl monooleate Polyoxyethylene glycerin fatty acid ester such as polyoxyethylene monoisostearate, polyoxyethylene monosoleate, etc .; Polyoxyethylene disozone fatty acid esters such
  • the zwitterionic surfactant '( ⁇ herbal agent (b 3) is at least one selected from the group consisting of betaine and amine oxides.
  • examples of the betaine zwitterionic surfactant include coco fatty acid amidyl pyrcarboxybetaine, lauric / redimethylaminoacetic acid betaine, and imidazolium betaine.
  • coco fatty acid amidpropylcarboxybetaine and lauryl dimethinoreaminoacetic acid betaine are preferred from the viewpoint of the stability of the above-described compound containing an antibacterial component in a solution.
  • aminoxide zwitterionic surface active agent examples include lauramide propinoresimetylaminoxide, lauryldimethylamine amine, and the like.
  • lauramidopropyldimethylamine oxide and lauryldimethylamine amine are preferred from the viewpoint of the stability of the above-mentioned silicon-containing compound which is an antibacterial component in the solution.
  • lauramidopropinolide dimethylamine oxide is the most preferable from the viewpoint of the long-term stability of the above-mentioned compound containing silicon in a solution. I like it.
  • an aqueous solution is usually employed as the solvent for the antibacterial agent spoilage used in the present invention.
  • the above-mentioned compound containing a silicon (a), a cationic surfactant (b 1) and Z or a nonionic surfactant As long as (b 2) and Z or a zwitterionic surfactant (b 3) are dissolved, it can be used as a mixed solvent of water and a hydrophilic solvent such as methanol, ethanol, propanol, or acetone.
  • the antibacterial composition is composed of a single compound containing a silicon (a) as an active ingredient.
  • the content of the silicon-containing compound (a) in the antibacterial agent composition is usually 0.01 to 60% by volume, preferably 0.1 to 10% by volume. It is preferable to be in this range in order to fully exert its cleaning action, antibacterial action and its sustainability.
  • the antibacterial agent and the above-mentioned antibacterial agent composition are active ingredients such as a compound (a) and a cationic surfactant (excluding the above-mentioned compound containing a silicon), nonionic surfactant '
  • a compound (a) and a cationic surfactant excluding the above-mentioned compound containing a silicon
  • nonionic surfactant '
  • the content of the key compound (a) in the antibacterial composition is usually 0. 01 to 40% by volume, preferably 0.1 to 10% by volume
  • the surfactant (b) content is usually 0.007 to 20% by volume, preferably 0.05 to 10% by volume. Yes, it is preferable to be in this range in order to fully exert the cleaning action, antibacterial action and its sustainability.
  • the treatment with the antibacterial agent composition of the article before and after the treatment such as ozone water described above is performed by applying the antibacterial agent composition to the surface of the article or applying the antibacterial agent composition to the surface of the article.
  • the fogging force, washing the surface of the article several times with the antibacterial agent composition (cleaning), or wiping the surface of the article with a cloth soaked with the antibacterial agent composition The method is not particularly limited as long as the article and the antibacterial agent composition can be repelled for a predetermined time.
  • the time for performing these treatments may be any time as long as the antibacterial component contained in the antibacterial agent composition can sufficiently react with the surface of the article.
  • the treatment with the antibacterial agent composition is performed as described above.
  • the antibacterial agent composition after treatment with the antibacterial agent composition:!
  • the microwave mouth wave irradiation treatment of ⁇ 10 GHz after the microphone mouth wave irradiation treatment, the antibacterial agent composition may be removed from the surface of the article by washing with water as necessary. . [0 0 7 1]
  • Articles having antibacterial agents fixed on the surface by the antibacterial agent fixing method of the present invention include dental materials such as implants, crowns, bridges, orthodontic brackets, and dental wires, tableware, glasses, sinks, and kitchens.
  • dental materials such as implants, crowns, bridges, orthodontic brackets, and dental wires, tableware, glasses, sinks, and kitchens.
  • the article treated by the antibacterial agent immobilization method of the present invention includes the article in the antibacterial agent composition. Even if the antibacterial cage-containing compound is made of a synthetic resin which is difficult to bind, it has very excellent antibacterial performance and its durability.
  • the material constituting the article is not particularly limited. According to the method for immobilizing an antibacterial agent of the present invention, excellent antibacterial performance can be obtained even for various materials such as glass, ceramics, ceramics, metals, and synthetic resins. And its life can be granted
  • the antibacterial agent is immobilized on the antibacterial agent by pretreatment with ozone water or microwave irradiation (microwave oven).
  • ozone water or microwave irradiation microwave oven
  • Bacteria used for the antibacterial test are Candida 'C. albicans strain GDH18, pre-cultured in Sabouraud medium for 18 hours, and 1 ⁇ 10 6 cells / mL in ultrapure water (MQ water). Adjusted.
  • a sample piece of 1 x 1 cm square Atari Nore plate was produced by a master of ozone sterilization (manufactured by Ozone Total System Co., Ltd.) in 0.4 to 0.6 ppm ozone water approximately 30 mL for 5, 10, 15 minutes After soaking, drain the water with filter paper and remove each sample piece from octadecyldimethyl (3-trimethoxysilylpropyl) ammonium chloride (Si-QAC) (3% (capacity Z capacity)) and polyoxyethylene.
  • Si-QAC octadecyldimethyl (3-trimethoxysilylpropyl) ammonium chloride
  • Si-QAC octadecyldimethyl (3-trimethoxysilylpropyl) ammonium chloride
  • P0 sorbitan monolaurate
  • Microphone mouth wave irradiation treatment Microwave oven treatment 1
  • a 1 x 1 cm square acrylic board for 30, 60, 90 seconds in a household microwave oven (output 700W, manufactured by National, product name: microwave oven NE-EZ2, microwave: 2.450GHz)
  • output 700W manufactured by National, product name: microwave oven NE-EZ2, microwave: 2.450GHz
  • Si-QAC 3% (capacity / capacity)
  • P0 1% (capacity / capacity)
  • Microwave irradiation treatment Microwave oven treatment 2
  • a 1 x 1 cm square acrylic plate was immersed in a mixed aqueous solution of Si-QAC (3% (volume capacity)) and lauramide propyldimethylamine amine (LAO) (1% (volume Z capacity)). After that, immediately after the treatment with a microwave oven 700W for 30 seconds or 500W for 20 seconds, it was immediately washed with water and used as a test piece for antibacterial test.
  • Si-QAC 3 (volume capacity)
  • LAO lauramide propyldimethylamine amine
  • Each test piece obtained as described above is inoculated with 25 // L (2500 pieces) of Candida albicans bacterial solution that has been adjusted to 1 X 10 6 cells / mL in advance and left for 2 hours. Waiting for settling. Thereafter, 1 mL of Sabouraud medium (Fuji Pharmaceutical Candida Yellow medium) containing chlorophenol red as a pH indicator was added and cultured at 37 ° C for 48 hours. Next, ATP was extracted from the bacteria grown on the surface of each test piece, and quantified. Extraction of ATP was performed by immersing each test piece for 30 minutes in 500 x L of Toa Denpa Kogyo Co., Ltd. «Biological ATP extraction reagent AF-2K1. The amount of ATP was measured by setting the obtained extract in a cell timer glow manufactured by Tuner Biosystems.
  • Figure 1 shows the results of the antibacterial test.
  • the ones that were not treated with ozone water or the like and treated with Si-QAC (1% (volume / volume) P0) solution and those treated only with Si-QAC solution were used. .
  • Fig. 1 shows the amount of ATP (pmol) per sample, and ATP lpraol corresponds to about 100 bacteria.
  • Si-QAC-free the treatment with Si-QAC solution
  • Si_QAC present the bacteria grew to 4 ⁇ 10 6 cells.
  • the growth was suppressed to about 1/3 ⁇ 1 ⁇ .
  • Bacterial growth was further suppressed compared to test specimens treated with Si-QAC solution without treatment with water or the like. More specifically, no fungal growth was observed when the ozone water treatment was performed for more than 5 minutes or the microwave treatment was conducted for 0.5 minutes.
  • Denture base acrylic resin (trade name: Akron MC, manufactured by Gichi Co., Ltd.) was polymerized as usual to prepare a 10 x 10 x 0.2 mm sample piece.
  • the test surface was a glass pressure contact surface.
  • Bacteria used in the antibacterial test are Candida albicans strain GDH18, pre-cultured for 18 hours in Sabouraud medium, and 1 ⁇ 10 6 cells / mL with ultrapure water (MQ water). Adjusted.
  • each sample piece After immersing the sample piece in about 30 mL of 0.4 to 0.6 ppm ozone water produced by a master of ozone sterilization (Ozone Total System Co., Ltd. 3 ⁇ 4h) for 0, 1, 3, 5, 10 minutes, put it on the filter paper. After draining, each sample piece is immersed in a mixed solution of Si-QAC (3% (capacity Z capacity)) and P0 (1% (capacity Z capacity)), then washed with water and used for antibacterial testing. A test piece was obtained.
  • Si-QAC 3% (capacity Z capacity)
  • P0 1% (capacity Z capacity)
  • Figure 2 shows the results 12 hours after the start of culture.
  • the medium turns yellow, and the bacteria are growing at 1 X 10 8 cells / raL or more, but after treatment with ozone water for 0, 1, 3, 5, 10 minutes.
  • the test piece treated with a mixed solution of Si-QAC and P0 no growth of bacteria was observed.
  • the sample treated for 1 minute is orange, and the bacteria are growing on the order of 1 X 10 5 cells / mL.
  • Figures 3 and 4 show the results 18 to 36 hours after the start of culture.
  • Figures 3 and 4 show that in the sump / res treated for 0, 1, and 3 minutes, the medium turned yellow after 36 hours and that the bacteria had grown to more than 1 X 10 8 cells / mL. Of the 2000 inoculated, approximately 50-100 were considered alive. In contrast, the specimens treated with ozone water for 5 to 10 minutes and then treated with Si-QAC solution showed no growth of bacteria after 18 hours, but those treated for 5 minutes It appears orange after 36 hours, and it is probable that several bacteria remained.
  • Fig. 5 shows the results 48 hours after the start of culture
  • Fig. 6 shows the results one week after the start of culture. From Fig. 5, the state of each sample is almost the same after 48 hours from the start of the culture. However, as shown in Fig. 6, when treated with ozone water for 10 minutes, the growth of the bacteria can be achieved even after one week. It is considered that all the inoculated bacteria were killed.
  • a cover glass for a hemocytometer was used as a test piece.
  • Bacteria used in the antibacterial test were Candida 'C. albicans strain GDH18, pre-cultured in Sabouraud medium for 18 hours, and then 1 ⁇ 10 5 cells / mL in ultrapure water (MQ water). It was adjusted.
  • controllers there are two types of controllers, one that is immersed in ultrapure water and then immersed in 5% EtAC (3% (volume / volume)) 70% ethanol solution for 5 minutes, and the other that is only immersed in ultrapure water. Sighed.
  • the medium appears red in all conditions, and the antibacterial agent immobilization treatment using any of the solutions can sufficiently suppress the growth of the bacteria for 24 hours after inoculation. Conceivable.
  • the color changed slightly to orange.
  • Figure 7 shows the results 33 hours after the start of culture.
  • Table 1 shows the notation of each solution and control in Fig. 7 (and Fig. 8 to be described later).
  • Example 3 the treatment time with EtAC was as short as 5 minutes at room temperature. Therefore, it is considered that the antibacterial activity was hardly observed in the control without the ozone water treatment.

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Abstract

L'invention porte sur un procédé de fixation d'un agent antibactérien par lequel d'excellentes propriétés antibactériennes et un entretien de celles-ci peuvent être conférés à une large gamme d’articles comportant ces matériaux. Le procédé de fixation d'un agent antibactérien est caractérisé par le fait qu'il consiste : à soumettre la surface d'un article à un traitement de surface grâce auquel un groupe fonctionnel contenant de l'oxygène est conféré à celle-ci, et (a) à traiter l'article à l'aide d'une composition antibactérienne qui comporte un composé contenant du silicium, représenté par la formule générale (1), (dans laquelle R1 représente un groupe hydrocarboné ayant au moins 6 atomes de carbone, R2 et R3 peuvent être soit identiques soit différents et représentent chacun un groupe hydrocarboné inférieur, R4 représente un groupe hydrocarboné inférieur divalent, R5, R6 et R7 peuvent être soit identiques soit différents et représentent chacun un groupe alkyle inférieur ou un groupe alcoxy inférieur, et X représente un ion halogène ou un ion carboxyloxy organique), ou à traiter celui-ci par la composition antibactérienne décrite ci-dessus, en faisant suivre par une irradiation par micro-ondes de 1 à 10 GHz, tout en permettant à la composition antibactérienne telle que décrite ci-dessus de rester sur la surface de l'article.
PCT/JP2009/058229 2008-05-09 2009-04-21 Procédé de fixation d'agent antibactérien et article obtenu par le procédé WO2009136561A1 (fr)

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US12/736,794 US8859009B2 (en) 2008-05-09 2009-04-21 Method of fixing antibacterial agent and article obtained by the method
CN2009801270768A CN102105062A (zh) 2008-05-09 2009-04-21 一种固定抗菌剂的方法及由该方法获得的产品
JP2010511046A JP5618370B2 (ja) 2008-05-09 2009-04-21 抗菌剤固定化方法および該方法により得られる物品
AU2009245152A AU2009245152B2 (en) 2008-05-09 2009-04-21 Method of fixing antibacterial agent and article obtained by the method
KR1020107027749A KR101681522B1 (ko) 2008-05-09 2009-04-21 항균제 고정화 방법 및 상기 방법에 의해 얻어진 물품

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010073825A1 (fr) * 2008-12-25 2010-07-01 国立大学法人広島大学 Composition antibactérienne et composition antivirale contenant chacune un composé silicié, méthode d'antibactérialisation, procédé de nettoyage/nettoyage de la cavité buccale, et procédé d'immobilisation d'un agent antibactérien ou d'un agent antiviral
JP4611445B1 (ja) * 2010-01-19 2011-01-12 株式会社テラモト 表面多機能処理剤組成物
JP4611446B1 (ja) * 2010-01-19 2011-01-12 株式会社テラモト 表面多機能処理剤組成物
WO2013047642A1 (fr) * 2011-09-29 2013-04-04 Ｔｂカワシマ株式会社 Article comportant un agent antibactérien immobilisé et son procédé de fabrication
JP2014524980A (ja) * 2011-07-08 2014-09-25 スペシャルティ コーティング システムズ， インク． 抗菌性パリレン・コーティング及び同コーティングを蒸着する方法
JP2018150631A (ja) * 2017-03-09 2018-09-27 株式会社川島織物セルコン 機能性繊維物、機能性繊維物の製造方法、及び、機能剤

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2431173B (en) * 2005-09-15 2010-01-13 Alexium Ltd Method for attachment of silicon-containing compounds to a surface
GB201108806D0 (en) * 2011-05-25 2011-07-06 Arcis Biotechnology Ltd Plant treatment method
GB201108797D0 (en) * 2011-05-25 2011-07-06 Arcis Biotechnology Ltd Surface treatment method
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CN105435657B (zh) * 2014-07-22 2018-01-23 中国石油化工股份有限公司 一种复合纳滤膜及其制备方法
US10980236B2 (en) 2014-11-04 2021-04-20 Allied Bioscience, Inc. Broad spectrum antimicrobial coatings comprising combinations of organosilanes
US10993441B2 (en) 2014-11-04 2021-05-04 Allied Bioscience, Inc. Antimicrobial coatings comprising organosilane homopolymers
JP2021070672A (ja) * 2019-11-01 2021-05-06 ジェクス株式会社 害虫忌避剤
CN111592946A (zh) * 2020-06-05 2020-08-28 上海和黄白猫有限公司 一种抗菌洗衣液及其制备方法

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6248601A (ja) * 1985-08-27 1987-03-03 Takeda Chem Ind Ltd 殺菌消毒剤
JPH11246310A (ja) * 1998-02-25 1999-09-14 Showa Kk 殺菌剤
WO1999056714A1 (fr) 1998-04-30 1999-11-11 Kyowa Limited Bactericide pour detergent
JP2001288062A (ja) 2000-03-31 2001-10-16 Kobayashi Pharmaceut Co Ltd 義歯洗浄剤
JP2003145669A (ja) * 2001-11-08 2003-05-20 Matsushita Electric Ind Co Ltd 防汚性被膜を有する物品およびその製造方法
JP2004209241A (ja) 2002-12-16 2004-07-29 Hiroshima Univ 抗菌性材料、及びその製造方法
WO2007031775A1 (fr) * 2005-09-15 2007-03-22 Alexium Limited Procédé pour la fixation de composés contenant du silicium sur une surface et pour la synthèse de composés de silicium hypervalent
JP2007146134A (ja) 2005-11-04 2007-06-14 Hiroshima Univ 洗浄剤組成物、洗浄方法および被洗浄物品

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3472900A (en) * 1966-07-18 1969-10-14 Baird Chem Ind Preparation of trialkylamines
JP2000290405A (ja) 1999-04-08 2000-10-17 Shinko Plant Kensetsu Kk 高分子材料の表面処理方法
JP2001329088A (ja) 1999-10-18 2001-11-27 Nippon Sheet Glass Co Ltd 二酸化珪素被覆ポリオレフィン樹脂及びその製造方法
US20030065292A1 (en) * 2001-06-08 2003-04-03 Darouiche Rabih O. Ozonated medical devices and methods of using ozone to prevent complications from indwelling medical devices
US20060134163A1 (en) * 2004-12-16 2006-06-22 Bagwell Alison S Immobilizing anti-microbial compounds on elastomeric articles
US8999363B2 (en) * 2005-02-07 2015-04-07 Sishield Technologies, Inc. Methods and compositions for antimicrobial surfaces
JP5464784B2 (ja) 2005-10-05 2014-04-09 日本曹達株式会社 基材をオゾン水又は過酸化水素水で洗浄する工程を含む、有機薄膜の製造方法
JP4895261B2 (ja) 2005-11-04 2012-03-14 国立大学法人広島大学 合成樹脂の抗菌処理方法、抗菌性合成樹脂及びその製造方法、製造装置
EP1955764A4 (fr) * 2005-12-02 2012-08-15 Sekisui Chemical Co Ltd Microparticule polymère hydrophile, charge de remplissage pour la chromatographie liquide par échange d ions, et procédé de production de la charge de remplissage pour chromatographie liquide par échange d ions

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6248601A (ja) * 1985-08-27 1987-03-03 Takeda Chem Ind Ltd 殺菌消毒剤
JPH11246310A (ja) * 1998-02-25 1999-09-14 Showa Kk 殺菌剤
WO1999056714A1 (fr) 1998-04-30 1999-11-11 Kyowa Limited Bactericide pour detergent
JP2001288062A (ja) 2000-03-31 2001-10-16 Kobayashi Pharmaceut Co Ltd 義歯洗浄剤
JP2003145669A (ja) * 2001-11-08 2003-05-20 Matsushita Electric Ind Co Ltd 防汚性被膜を有する物品およびその製造方法
JP2004209241A (ja) 2002-12-16 2004-07-29 Hiroshima Univ 抗菌性材料、及びその製造方法
WO2007031775A1 (fr) * 2005-09-15 2007-03-22 Alexium Limited Procédé pour la fixation de composés contenant du silicium sur une surface et pour la synthèse de composés de silicium hypervalent
JP2007146134A (ja) 2005-11-04 2007-06-14 Hiroshima Univ 洗浄剤組成物、洗浄方法および被洗浄物品

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HIROKI NIKAWA: "Hoteibutsu no Kokin Coat-zai 'Nikabaiogado' -sono Koka to Tokucho ni Tsuite", NIPPON DENTAL REVIEW, vol. 66, no. 10, 11 October 2006 (2006-10-11), pages 103 - 110, XP008150056 *
See also references of EP2274985A4

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010073825A1 (fr) * 2008-12-25 2010-07-01 国立大学法人広島大学 Composition antibactérienne et composition antivirale contenant chacune un composé silicié, méthode d'antibactérialisation, procédé de nettoyage/nettoyage de la cavité buccale, et procédé d'immobilisation d'un agent antibactérien ou d'un agent antiviral
US9609872B2 (en) 2008-12-25 2017-04-04 Hiroshima University Antibacterial agent composition and antiviral agent composition comprising silicon-containing compound; antibacterializing method, cleaning/mouth rinsing method; method for fixing antibacterial agent and antiviral agent
US9278107B2 (en) 2008-12-25 2016-03-08 Hiroshima University Antibacterial agent composition and antiviral agent composition comprising silicon-containing compound; antibacterializing method, cleaning/mouth rinsing method; method for fixing antibacterial agent and antiviral agent
JP2011148718A (ja) * 2010-01-19 2011-08-04 Teramoto Corp 表面多機能処理剤組成物
WO2011089839A1 (fr) * 2010-01-19 2011-07-28 株式会社テラモト Composition de traitement de surface multifonction
JP2011148717A (ja) * 2010-01-19 2011-08-04 Teramoto Corp 表面多機能処理剤組成物
WO2011089840A1 (fr) * 2010-01-19 2011-07-28 株式会社テラモト Composition de traitement de surface multifonction
EP2526772A1 (fr) * 2010-01-19 2012-11-28 Teramoto Corporation Ltd. Composition de traitement de surface multifonction
EP2526772A4 (fr) * 2010-01-19 2013-08-28 Teramoto Corp Ltd Composition de traitement de surface multifonction
JP4611446B1 (ja) * 2010-01-19 2011-01-12 株式会社テラモト 表面多機能処理剤組成物
JP4611445B1 (ja) * 2010-01-19 2011-01-12 株式会社テラモト 表面多機能処理剤組成物
JP2014524980A (ja) * 2011-07-08 2014-09-25 スペシャルティ コーティング システムズ， インク． 抗菌性パリレン・コーティング及び同コーティングを蒸着する方法
WO2013047642A1 (fr) * 2011-09-29 2013-04-04 Ｔｂカワシマ株式会社 Article comportant un agent antibactérien immobilisé et son procédé de fabrication
JPWO2013047642A1 (ja) * 2011-09-29 2015-03-26 Ｔｂカワシマ株式会社 抗菌性を有する剤が固定化された物品及びその製造方法
JP2018150631A (ja) * 2017-03-09 2018-09-27 株式会社川島織物セルコン 機能性繊維物、機能性繊維物の製造方法、及び、機能剤

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MY157613A (en) 2016-06-30

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